Insurance and hosting is the best he can come up with? I pay for BOTH of those on my own now despite being chained to a company for a paycheck.

Second. We're 2 guys. We started doing just fine at about 5k/month. I ran down his checklist going yep, yep, yep. I don't have my own jet or live a a half-million dollar house but its been far and away better on all fronts than the job I quit.

Too cautious is just as fail as not enough. (And less fun)